Acetic Acid → HCID 66941896, compound

HRID 348687Notes

Reaction equation

HRID 348687 reaction equation
[CH2:1]([O:8][C:9](=[O:41])[N:10]([CH:35]1[CH2:40][CH2:39][CH2:38][CH2:37][CH2:36]1)[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:34])[C:20]2[CH:25]=[CH:24][C:23]([CH2:26][NH:27][CH2:28][C:29]3[NH:30][CH:31]=[CH:32][N:33]=3)=[CH:22][CH:21]=2)=[CH:14][CH:13]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH:42]1[CH:46]=[CH:45][N:44]=[C:43]1[CH:47]=O.C([BH3-])#N.[Na+].C(O)(=O)C>CO>[CH2:1]([O:8][C:9](=[O:41])[N:10]([CH2:11][C:12]1[CH:13]=[CH:14][C:15]([NH:18][C:19](=[O:34])[C:20]2[CH:25]=[CH:24][C:23]([CH2:26][N:27]([CH2:47][C:43]3[NH:42][CH:46]=[CH:45][N:44]=3)[CH2:28][C:29]3[NH:33][CH:32]=[CH:31][N:30]=3)=[CH:22][CH:21]=2)=[CH:16][CH:17]=1)[CH:35]1[CH2:36][CH2:37][CH2:38][CH2:39][CH2:40]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 249551H-imidazole-2-carbaldehydeHCID 5003444Sodium cyanoborohydrideHCID 66941300HCID 66941300, compound

Product 1

HCID 66941896HCID 66941896, compoundYield 101.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound (242 mg) obtained in Example 87-4 and 2-imidazole carboxaldehyde (63.4 mg) were dissolved in anhydrous methanol (7.2 ml). Then, the solution was added with sodium cyanoborohydride (96.9 mg) and adjusted to pH 5 with acetic acid, followed by stirring at room temperature for 2 days. After the reaction, the solvent was distilled off. The residue was added with a 1 mol/l sodium hydroxide aqueous solution and extracted with chloroform. Subsequently, the extract was washed with saturated saline solution and the residue was then dried with anhydrous magnesium sulfate, followed by distilling the solvent off. The residue was purified through silica gel column chromatography (chloroform/methanol), thereby obtaining the subject compound (282 mg) as a white solid.

Workup

  1. customAfter the reaction
  2. distillationthe solvent was distilled off
  3. additionThe residue was added with a 1 mol/l sodium hydroxide aqueous solution
  4. extractionextracted with chloroform
  5. washSubsequently, the extract was washed with saturated saline solution
  6. dry with materialthe residue was then dried with anhydrous magnesium sulfate
  7. distillationby distilling the solvent off
  8. customThe residue was purified through silica gel column chromatography (chloroform/methanol)

Sources & evidence

ORD record
ord-bf90419b56424791b266586d6967b19e
Source dataset
uspto-grants-2007_02
Patent number
US07176227B2

Reaction notes

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